Congratulations on your new boat

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I bought my first Outfitter, an ex-rental boat, last summer and bought my second, a new one, this summer. I think the Oasis might be an overall superior boat, especially in its latest incarnation, but my transportation means requires that I stick with a smaller boat. Still, when running the Outfitter solo, and properly ballasted in the forward end, I can maintain 4mph for several hours in calm conditions and no current; its fast enough for me and I'm quite happy with both.
Reselling your's when the time comes shouldn't be a problem; they hold their value.
There are some good Hobie kayak sailing and sail modification videos on Youtube, there's the Sailing Forum here on this site, and there's the downloadable Hobie sailing pamphlet as well if one didn't come with your sail.
Keith